Decoding Startup Investment: SAFE Notes, Convertible Notes & Priced Rounds - podcast episode cover

Decoding Startup Investment: SAFE Notes, Convertible Notes & Priced Rounds

Mar 09, 202557 minSeason 1Ep. 37
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Episode description

Episode Summary:

Understanding how to invest in startups requires more than just writing a cheque. Cheryl and Maxine break down the legal structures behind startup investing, covering SAFE notes, convertible notes, and priced rounds. Whether you're a seasoned investor or just starting out, this episode unpacks the key terms, investor-friendly vs. founder-friendly clauses, and the risks involved.

They discuss the evolution of SAFEs, why they've become the dominant structure in early-stage funding, and the critical differences between pre-money and post-money SAFEs. Plus, they explore the role of pro-rata rights, most favoured nation (MFN) clauses, and side letters—so you don’t get caught off guard in your next deal.

If you’ve ever wondered how to protect your equity position, when to push back on certain terms, or what legal documents you’ll actually be signing, this episode is your investor cheat sheet.

Key Takeaways:

00:00 – Why startup investment structures matter

01:45 – SAFE notes, convertible notes, and priced rounds explained

03:47 – How founders raise money: equity vs. debt

06:21 – The documents you’ll sign in a priced round

10:22 – Do startups need a constitution? Red flags to watch for

14:29 – Side letters: What are they, and should you be worried?

19:08 – Pro-rata rights & why they matter for investors

22:23 – Most Favoured Nation (MFN) clauses explained

30:27 – Pre-money vs. post-money SAFEs: Which one is better?

38:03 – Why valuation caps and discounts can be a double-edged sword

43:53 – Investor-friendly vs. founder-friendly terms: What’s fair?

Resources

- A Deep Dive into ECIS, ESVCLP, and Investment Strategies - https://open.spotify.com/episode/1Agiu4dskF53m6DBZgXitD?si=KFeAlY_wTjSwOWfRMiiQFA

- Angel Academy – The most comprehensive angel investing course for Australia & NZ: www.venture.academy

- Aussie Angels – Cheryl’s platform for angel investing https://www.aussieangels.com/

- Co-Ventures – Maxine’s venture capital firm https://www.coventures.vc/

Sponsors:First Cheque is supported by our wonderful sponsors:

Aussie Angels makes it easy for accredited investors to back early-stage startups alongside experienced syndicate leads. With no platform fees and minimum cheques from $2,500, you can build a diversified portfolio of high-growth companies with confidence.

https://www.aussieangels.com/

Galah Cyber: Galah Cyber are perfect for founder-lead and SAAS businesses. Galah provides advice, education, and training. Get in touch with Galah Cyber for a complimentary call to make sure you’re secured.

https://dayone.fm/galah

First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often.

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Mentioned in this episode:

November 2024 - Galah Cyber

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Transcript

Cheryl and Maxine 00:00 Hey! Three, two, one. I'm Cheryl, and I'm Maxine. This is First Cheque, part of Day One—the network dedicated to founders, operators, and investors. If you want to be a better early-stage investor, this is the show for you. So, TLDR, if you don't want to suck at investing, listen up.

Cheryl 00:21 Alright, so this episode is going to get a bit technical, folks. Bear with us. We'll try to keep it as fun and interactive as possible as we can for a conversation about vaccines.

Maxine 00:40 We're talking legal terms, legal structures, and how you invest in startups. I actually reject the premise that it's boring. As a recovering corporate lawyer, I find this stuff super interesting. I nerd out on the mechanics of deals and for those out there who love this kind of stuff, I think it's fascinating to think about how the mechanics of getting money into businesses and the protections you put around them work. But I recognise I am in the minority that loves this kind of stuff. So for those who aren't super nerdy in this corner of their interests, strap in. For those who are ready for some serious legal nerd out with me, also strap in. We're going to be talking about SAFE notes, convertible notes, and priced rounds. The terms you usually see within them, some tips and tricks on navigating them, what you can expect to see, what is founder friendly, what is investor friendly, and, if we have time, maybe some spicy terms at the end that we've seen floating around. Should we dive in? Cheryl, do you want to set us up with some definitions? What is a SAFE? What is a convertible note? And what is a priced round?

Cheryl 01:45 Meanwhile, I'm on the other side of the fence where, like, I didn't even ask what SAFE stood for until probably the third or fourth one that I had signed. So, you know, that's me over here.

Maxine 01:54 That's sacrilege. I'm shocked. I don't even know what to say. If you're in the same bucket as me, team, don't worry. We've got you covered in this episode. First, it's important to note that when startups are raising, there are two buckets: there is equity and debt, and there are structures within one and structures within the other.

And then there's one that's kind of in the middle. So I'm going to go through the four main structures that startups usually raise with. First is priced equity, and that is essentially, I, as the investor, give the founder money, and they give me a piece of paper that says I get a certain number of shares immediately. The second one under that equity bucket is the SAFE note. And if you don't know what SAFE means, I do now; it stands for Simple Agreement for Future Equity. That one is, I give the startup money, and they give me a piece of paper that says I will own some shares at some point in the future. And the amounts and times vary, depending on a few factors that are in that SAFE note agreement. There are two subversions of the SAFE, which are the pre-money and the post-money, and we will get into those. Now, on the other side, on that debt side, we have your standard loan, which is I give you money, and you pay it back to me. And then the one that's kind of overlapping in the middle is this convertible note, or shortened to con note. And that is essentially, I give the founder money, and the founder gives me a piece of paper that says I will either get some shares in the future at some point in time, or they will pay me back with interest. Now, I say that it is kind of in the middle because it is written like debt, but it is generally the intention or the purpose is generally actually to get equity. So they're kind of overlapping there. So those are the four basic buckets of how startups raise and what you can invest in via a structure.

Maxine 03:47 Love it. You would never know that you didn't nerd out on these topics. You speak about them so eloquently.

Cheryl 03:54 Well, when you create a course all about this and we have a whole section on the Angel Academy course, then yeah, you get to know it pretty well and feel a lot more confident about what SAFE stands for now.

Maxine 04:05 100%. I love that it's the course creation, not the investing that got you over the line. But I think something to kind of anchor in on fundamentals, right? You said it there at the beginning, but I really want to repeat this. There are two ways and only two ways to put your money into a business. One is to buy equity. So to buy shares in that business and contribute to the equity of that business. Or two, to lend it money. As a shareholder, someone who owns equity in a business, you are part of the capital stack. Which means you were part of the owner group as someone who lends money to the business, i.e., as a debtor, you don't own the business. You have a purely contractual arrangement with that business that you have given the money, and they will give it back to you on some terms, usually interest. And so we are as investors talking about the process, even if it's kind of in a wiggly way via debt to buy shares in a business, either via buying them directly in a price round, buying them indirectly via a safe, which is essentially an agreement that you will get equity at some point in the future, as you said, or we kind of hedge our bets. We either take debt or equity depending on how badly it goes. Actually, have you ever seen a startup where they have converted the debt side? Yeah. As opposed to the equity side. I've never seen it.

Cheryl 05:31 Yeah, definitely later-stage startups for sure.

Maxine 05:32 Uh, yeah, yeah. Okay. So they use con notes between like for bridging rounds and then they use it as debt.

Cheryl 05:40 Yeah.

Maxine 05:40 Interesting. Yeah, I've never seen it. It's one of those phantom figures out there in the ecosystem that one day hopefully I will see.

Cheryl 05:47 Well, when you get to see as many deals as I do, we see it.

Maxine 05:52 Absolutely. So let's go one by one. Let's start with equity because I think that's a really good place to start because the other two are what we would call kind of derivative forms of equity, meaning you are buying a right to this fundamental thing sometime in the future.

Cheryl 06:02 Well, I feel like we don't need to do too much on the loan side, like loans are loans, right? Like you, you, yeah,

Maxine 06:04 yeah. We'll put loans in the bin.

Cheryl 06:07 Yeah, but let's start with equity because I think that's a good place to start because the other two are what we would call kind of derivative forms of equity, meaning you are buying a right to this fundamental thing sometime in the future.

Maxine 06:21 So let's start with equity. I think we call them convertible instruments. True. They are not derivatives. That is very true. Come on, Maxine. Legal terms. How am I the one telling you the proper legal term for safes and con notes? Convertible instruments.

Maxine 06:31 You are the expert. You're the expert in the room. Again, recovering corporate lawyer over here.

Maxine 06:57 So let's start with the priced round. So what are the instruments that we usually use? What are the documents we usually use to buy equity in an Australian business? And we should say, this is largely Australian, although noting that the safe does come from US origins. So what are the usual documents we're using to buy?

Cheryl 07:23 This is such an interesting one because genuinely it is confusing, and we get this mixed up I think as investors all the time like I'm five years into my angel investing journey, and it's taken me creating a course on this to actually really understand the lineage between like what's connected because I still will get investors saying like, Oh, you know, like I haven't signed the safe note or haven't signed the safe agreement yet.

And I'm like, you're investing in a priced round. There is no safe. Yeah.

Maxine 07:25 Womp.

Cheryl 07:25 But okay, you want to draw some direct lines here? Okay. So a priced equity round is basically like the term that we use to describe the round. And then the document that you actually sign that gives you the actual shares is generally a document that is called the subscription agreement.

Now it gets a little complicated because the safe is a safe note. So we call it a safe round. It's a safe structure, and then it's just a safe note, and that can be split between a pre-money safe or a post-money safe and then the same with the con note we tend to shorten it to like con note like that's the structure of the round I'm using the actual agreement you sign is the convertible note.

So. That's the like, if you want to go straight lines down, they're somewhat confusing because a lot of people tend to think, Oh, well, the safe note is the thing that we sign all the time. And I'm not sure how that got into our briviage, but just putting it out there, it is not the thing you sign all the time.

If it's a priced equity round

Maxine 08:20 or if it's a convertible note round,

Cheryl 08:21 or

Cheryl and Maxine 08:22 if it's a note round,

Cheryl 08:23 correct,

Maxine 08:23 you will only sign a safe. If you are investing on a safe round, if you think you're investing in a safe round and you get a subscription deed, you're not investing in a safe round.

Cheryl 08:32 Correct. The other thing with the priced equity round is you are often also signing a new shareholders agreement.

So, uh, you are often signing two documents if you're doing a priced equity round versus if you're doing a safe round, it's usually only one document, which is that safe note.

Maxine 08:46 Absolutely. You also might get, uh, two additional documents as part of a price round. One is the constitution. So you'll get a copy of what the constitution is and the two documents that govern you as, or the main documents that govern you as a shareholder is your shareholder agreement, so the thing that you signed, and your constitution.

It's helpful to note here kind of what is generally in these documents as an overarching principle. I'm obviously not going to go into. NerdAlert, uh, and talk about all of those pieces, but a couple of things to name that are in these documents. They broadly cover who can manage the organization, right, what the directors can do, how many of them there can be, how they need to meet, how they may need to make decisions, how the shareholders can meet, what they need to make decisions on, how many of the shareholders there can be sometimes.

It also generally governs how The company is supposed to be managing certain key activities. And then you will also see in there, if it gets more complex things around each investors, a whole bunch of other complex stuff, but crucially, especially for the angel investors on this call, really understanding the mechanics of how this business is going to be run and commitments that either.

Uh, all of the directors are making or also the owners are making together on what they can do and what they can't do and the circumstances in which they need to share information with each other, the circumstances in which they need to sign things, the circumstances in which they need to agree to certain things.

All of those rules of engagement will be in your constitution and in your shareholders agreement. The fourth document that you might see floating around or that might be out there is something called a side letter.

Cheryl 10:22 Maybe let's just go back to constitution for a moment. Sure. Because, in Australia, I have met and invested in a number of startups that don't have a constitution and I never read one before.

In fact, I still really haven't read a constitution, guys. I have lawyers for that. But, in the very, you know, probably the first four or five companies I invested in, no constitution was handed to me. We don't necessarily actually have to have one in Australia. I don't know about the US, if that's a thing, and maybe you can comment on that.

But if you don't have a constitution, your constitution just defaults if you're a company to the Australian Corps Act. What are your thoughts on like, do you think startups need to have a separate constitution? And if so, at what point? Or like, is it from the beginning? Like, is it a red flag for you if they don't have one?

Maxine 11:06 Uh, yes, but like, it's like an amber flag if they don't have one. Um, there's a lot of standard terms. So they're called the replaceable rules. They're contained within the corporations act. Um, so if you want to know that you can just Google them and it will show you the section of the corporations act that has that.

all of that information in it. It's an amber flag for me because there's a lot of rules or kind of default terms in the constitution that are not super fit for purpose when it comes to startups, but more importantly there's a whole bunch of stuff around like the way that the company is governed.

Clarity on, you know, who gets to decide what and when that we see built into the constitutions when they are written out. Clarity on, you know, what do we do if there's a bad lever, for example. What do we do in the circumstance where we might have someone who is incapacitated? Um, what do we do with their shares?

Isn't that all covered in the shareholders agreement though?

Cheryl 12:04 Like bad lever, good lever, those are generally covered.

Maxine 12:07 Yeah, so across these two documents, right? Both of them will be, all of these terms are either covered in one or the other. The two should be read together as your, like, rules of engagement.

They're not in the replaceable rules. Sometimes you'll put them in the constitution and they won't be as robust. Shareholders agreement and sometimes there will be in the shareholders agreement.

Cheryl 12:24 So would that turn to a green flag for you if the things that like you feel aren't well covered in the corps act are covered in the shareholders agreement and they don't have a constitution?

Maxine 12:34 Yeah, that's it. Yes, it would turn into a green flag for me. It's an interesting legal question. I don't know. And maybe any of my fellow legal nerds out there in the ecosystem can I have a small kind of law school bell going off something to the extent that there's some hesitation about terms going in the shareholders agreement, which is a contractual agreement versus going in your constitution, which is.

It's covered under the Corporations Act, there might be kind of different ways that you're protected, but that is too deep legal nerd for me to go into, but it is also an indication, the other reason that it is an amber flag for me, it's also an indication that their team is kind of Not paying appropriate attention to the importance of these foundational documents of their organization.

It usually means that they are brazing around without any legal support at all, which is not something that I would suggest. There's loads of legal providers that will do a very cost-effective legal support for a safe round. And so I would encourage you to at least have a single conversation with a lawyer about those fundamentals.

What are you talking about? You often, you invested the, like, earliest pre CDC. Oh, yeah. Like, before the company's even formed. What are you talking about? Of course, like, don't you invest before that exists?

Maxine 13:49 Yeah, but I wouldn't suggest that you go through incorporation without any conversation with a lawyer as someone who has no legal background.

Cheryl 13:56 So you're fine if it comes later?

Maxine 13:58 Oh, yeah. You can invest as long as it comes later, okay.

Maxine 14:01 I can't invest into a company that doesn't exist yet. It needs to be incorporated for me to put money into it by buying said shares that we're talking about. So I'll commit. Right. Okay. Prior to that. But in order for me to finalize my investment, I need an entity to buy.

Cheryl 14:29 Right. Right. Cool. Yes. Buying shares. Got it. Fundamentals. You cannot invest in a company unless you buy shares. Otherwise, it's just debt. No. Safe. Well, or right to future shares or right to future. Yeah, right to future shares, but there is still something you need to be able to buy.

Cheryl 14:41 Yes. All right. So the other thing that you may or may not get slash sign in a deal, a side letter. So these are contracts that float around to put certain contractual terms between key people or key members of the deal. So you'll often see a side letter with the major investor. And the company, but not necessarily terms that are shared with everyone else. And so I think this is worthwhile naming. You will see a side letter alongside a safe note and also alongside a convertible note.

There's no reason you can't enter into a side letter with a company as part of an investment for any of these styles of investments. And essentially it is a either one to one or just a handful of investors are all signing up to certain additional terms on top of the. I will say here we saw a lot of these float around in 23, 24, for actually growth stage rounds.

There are some side letters out there that vary the terms that everyone else is investing on quite materially. So you'll often see ratchet or double ratchet clauses going in on the side letter as opposed to going into the core documents. And they're just being applied to a single investor as part of a round, as opposed to

Cheryl 15:47 Which is kind of scary, right?

Like as an investor for me, not to know what to Horrifying. Horrifying. I think is how I would describe that. Right, okay. Good to know my fear is justified. But like, to not know what other terms are out there, like, it makes me think, possibly should have, like, requested to know, like, what other side letters have you agreed to with other investors?

And if you enter into another side letter after this, then you have to tell

Maxine 16:14 me. The after the fact bit is interesting. I'll come back to that in a second, but for, I mean, for our diligence checklist, for example, as a question, we ask what prior contractual arrangements, as well as prior investment arrangements, have you already committed to on behalf of the company?

And so that we know kind of what the terms are that are floating around after the fact, you don't really have. Any ability to ask them to tell you what's coming in. With those double ratchets, I think they apply on top of you in the capital stack. And so they wouldn't necessarily dilute you down. I actually don't know.

That's an interesting question, the mechanics of that. Again, if there is any legal nerd listening, we would love you to comment on this.

Cheryl 16:52 I think a lot of this stuff matters in later rounds though, right? These are later rounds, yeah. These are growth stage

Maxine 16:56 terms.

Cheryl 16:57 Yeah, these are growth stage terms. Like, we're not going to be seeing startups having these terms in their, like, safe pre seed, seed rounds.

No, good God, no. So it's not something that, like, I'm not saying don't worry about it at all, but the risk is a bit mitigated by investing earlier stage.

Maxine 17:13 Correct. But we do see certain terms frequently pop up in side letters.

Cheryl 17:17 In side letters. Yeah, absolutely. Pro rata. I see that one in the side letter all the time.

And most favourite nations sometimes will be in that one as well. We also like, as a trust, we have like a limit of liability that goes into the side letter. Yep.

Maxine 17:32 Often there are information rights, right? I think that is often one that pops up. So for the bigger funds, they need the ability to be able to disclose key information back to their LPs and for compliance reasons.

And so they will put that in a side letter as opposed to put that in your, uh, Actually, I think often they do put this in the constitution or in, The shareholders agreement, um, if there is one or in the subscription agreement, if there is one, or in the later ones or in the safes and the con notes, they will put it in the side letter.

So I wonder if you want to tell us a little bit about pro rata, what is it as a term? Tell us a little bit about most favoured nation. What is it as a term? Pro rata

Cheryl 18:08 applies to both priced equity, as well as safe and con notes. Although it's worth noting that Like technically because you don't own shares at the time with safe or con notes that like pro rata is kind of debatable And so that's why it sometimes will go into the side letter just specifically say the next round you do any round Regardless of whether it's priced or another safe or whatever we get them But yeah, pro rata is essentially just saying and also in Australia, it's often called preemptive rights I'm not sure where they got that one from but pro rata Preemptive, and there's probably one other version of it, but it essentially means that you as an investor have a right to maintain your equity ownership in a future round.

So let's say the startup raises 500k and you invested 100k of that, which is 20 percent of the holdings, and then you now own 5 percent of the company. You know, don't math my math, but

Maxine 19:08 I'm using my calculator over here. I'm ready

Cheryl 19:08 for this example, using for simplicity purposes, then let's say the next round they go and they raise a million dollars.

And in that example, they are giving away, let's say 20 percent of their business. You would have a right to purchase up to a certain amount that would allow you to maintain that 5 percent of equity that you currently own. Um, sometimes that's. Uh, is a lot. Sometimes it's just a little, it really depends on the round size and the terms, but uh, pro rata just means that you are able to maintain your equity.

Maxine 19:40 Great. Also commonly known as anti dilution provisions. I knew there was a third one. You are trying to make sure that you don't get diluted down as more capital comes in over the top. And so it is the pro rata amount that you will hear investors like us talk about having. Kind of follow on capital, ready to go.

Sometimes you have opportunities to do a super pro rata, i. e. buy more ownership over time. And you will talk here. Some investors talk about that strategy, right? They seek to, to write a FOMO check or a learning check in at the beginning. And then they actually want to buy more of the business as they go.

And so this actually is the strategy that sits behind why you see. bigger fund managers seeding smaller funds because it gives them a diversified learning check into a bunch of companies. And then they will try and lean in and buy more of that company over time. You will see either pro rata or super pro rata in those side letters that you essentially is allowing those investors to maintain their dilution.

Offset it slightly or buy even more of the company as they go. What about Most Favoured Nation? Shortcut, it's not the UN.

Cheryl 20:51 So Most Favoured Nation, or it's sometimes shortened to MFN, is something that only applies to safe notes or con notes. And it basically says that if I sign a safe note with you and then you go and sign another one with someone else that has better terms than what I got, then my terms default to that.

What's interesting there is that, like, it is something that protects investors. There's also a presumption that the, like, investors that ask for it are basically saying that, you know, I believe that you may go and give another investor better terms than you're giving me. And, and I. I want to preempt that.

There are lots of situations where this comes up naturally, but the, like, the thought process of saying, like, I kind of don't trust you to keep the terms the same, I think is a really interesting version of, like, hey, let's, You know, sign a prenup, like that's the negative version of looking at it. It is definitely more investor friendly and so we tend to see it come out more during times when it is more difficult to raise.

And that is also just a factor of if it's more difficult to raise, you might be more likely to agree to more favorable terms to a different investor. I think what happens, I've, I don't know if I've ever actually seen one Play out where like they, I'm pretty sure if it would come to light during the conversion, so then you would like, you know, they might not know it until it goes to convert and then that would kick in and they would all like both safes, for example, if there were two of them would convert at the better one.

Maxine 22:23 Yeah, I think that's right. You, everything comes out in the conversion, right? Once you know that price per share, everything is revealed. I actually think that the most favoured nation clause, true, if it's, I mean, if it's coming purely from a face, a place of like not trusting, odd, but I think there is some very real reasons why you would include a most favoured nation in the circumstance of stacked safes.

And I can understand that it is more popular during tough times because in a stacked safe scenario. If you, say, enter in at a 10 mil pre and then they aren't able to raise and they go and raise at a 5 mil pre The dilution on you is savage And so what it allows for is to try to protect against that kind of essentially a down round Later on it's definitely an investor friendly term, but I think it's not just about Oh, you're going to kind of stitch me up, raise on an outrageously high valuation and then go and like sell it to all of your mates for a much lower valuation.

That's the kind of low trust interpretation, but I think the higher trust is more like it's kind of like the safe equivalent of a liquidity preference. Right, to make sure at least in the next round, you don't get

Cheryl 23:33 policed. You know what I think is interesting is that YC, which is the accelerator that originally invented the safe, they originally, the very first one they came out with was just a pre money safe and they updated their like template documents that they provide to the world and all of us.

YC. Um, excellent. Thank you. Thank you. They updated theirs. Oh, I don't know. It was, it like four or five years ago. And one of the, so it used to be just the pre money safe. Now there's three, uh, it is either Valcap, uh, no discount discount, no Valcap. Or, and this is interesting for this MFN conversation, the third one is just an MFN, no discount, no bow cap, which is interesting in the scenario that you can say, all right, well, I'm just going to invest and give you money and let someone else set the terms.

So here, take my 100k and the only thing we'll have in there that will determine how much I get in the future is this most favoured nation clause that says, when you go set terms with someone else, I will get those terms.

Maxine 24:32 Wow. I actually didn't know that that was a third. It's like the ugly stepsister of the other two.

Cheryl 24:39 I have seen that though. I have. I've seen it. You've seen it?

Maxine 24:43 Yeah. One of my

Cheryl 24:44 portfolio companies, I got investment from a prominent, uh, angel something. And with the understanding, they're like, well, you're probably going to go raise the next round. So just like, give me whatever terms they have.

Maxine 24:56 Interesting. I would imagine the only reason that you would do that, if there's no discount and no cab, the only reason you would do that is you are wanting, actually, this is probably a useful point to talk about one of the major benefits of both a safe and a convertible note, is they are much easier to be able to do.

And execute because you literally have the document that you have got from YC or some of the lawyers here in Australia from Airtable, I was going to call them Airtable, Airtree. Airtree or AIC. AIC, um, those standard documents, so it's much easier for you to get started. Yeah, you're only

Cheryl 25:32 negotiating like three things.

Maxine 25:34 So, and then you can roll that capital into the company, meaning you can roll safes, you can, you can close safes and bring that capital in as the same time as you are closing more safes. Yeah. The only time I would imagine that a most favoured nation would make sense is if you as an investor are expecting this founder to do a kind of rolling close and you are literally want the first or second person to write a cheque.

If you are thinking that they're going to hold on to that say for like a year at a time. And then close someone in a year, that would make no sense because you get absolutely no compensation for the like, period of de risking that they have done. So, I would imagine, hopefully, it's just those ones, like operator angels looking to like, get early capital in.

Cheryl 26:12 And to get in before a round gets filled, probably.

Maxine 26:15 Yeah, yeah. Very interesting. So, last bit on priced rounds, and then let's talk about safes because we've kind of covered everything else. The last thing I'll say on price rounds is one of the major downsides of kind of hinted to it. That is you have to close it all at once. You can sometimes do two closes, but that's idea because it's essentially all of these documents are being signed at once.

So all of these investors will have to sign at once. All of the money has to come into the accounts at once, which means. It is much more to coordinate to happen all at once and is also kind of single point of failure. So when you hear people's rounds falling over or, you know, rounds being pulled at the last minute, this is what they're talking about.

They're doing a priced round and everyone's ready to go and then someone key pulls out. And then someone else key pulls out and then everyone pulls out and then it's a really bad situation for the team. So price rounds, you have to close all at once. You have to, as an investor, you have to be ready to sign in a window to be able to do the close for the company, as opposed to the safe and the convertible note where you can.

Cheryl 27:19 I think for like from an investor perspective, it's helpful to understand why founders often will push for safes because obviously if given a choice any day of the week, I'm, I'm going to say, yeah, I'll take a price round over a safe note. Right. But I understand that for founders to, to essentially pull a price round together, there's more to negotiate.

It takes longer. There's more cats, there's more herding, there's more coordinating and like there's just more. Right. And so if you're in early stage, there's also more lawyers. There's more lawyers. There's which,

Maxine 27:52 which means it costs you a lot more. Don't forget those lawyers. We charge like wounded bulls.

Cheryl 28:00 I've

Maxine 28:00 never heard

Cheryl 28:01 that term. Yeah. So, so as an investor, you kind of have to understand why founders want to, to take your money on a safe note because you can sign and send money that day and no one else needs to be involved. Theoretically, right. You might still want to get lawyers involved, but it's just, it's a lot less work, which.

In turn is good for you as an investor means that they can spend more time on running the company rather than wrangling a bunch of investors to all sign at the same day,

Maxine 28:28 right? Yeah, absolutely. Especially in the pre-seed round, I often suggest to founders when they come and say that they're planning on raising a price round for their pre-seed.

Right? Especially if it's kind of anywhere between 500 to 750 K. The rule of thumb is you're spending like somewhere between 50 on legals for a price round. And so you don't want to be raising 500 and then passing 80 of that back to your lawyers. Like that does not make sense.

Cheryl 28:52 Really? I, that sounds high.

I, I would say the average is more like 30.

Maxine 28:58 Oh, interesting. That's the price in the U. S. Maybe it's come down since the last time I had to try and engage a lawyer, but it's not cheap, right? It's still a significant amount of capital.

Cheryl 29:07 No, still 30 grand is

Maxine 29:09 going out the door. And if you're only raising 500k, it's a material percentage of the amount raised.

Whereas in Australia, I'm seeing lawyers do it anywhere between kind of five and 10 for a safe or a con note. So anyway, it's much more cost-effective and percentage of capital going into proving out the business is much higher if you do it via a safe or a convertible note. So let's talk about safes.

What are the structures of them? What are the key terms that you would expect to see in one?

Cheryl 29:34 Yeah, safes are fun because like I said, there's only a couple terms you really need to go to negotiate and depending on which one you choose, then like even less. So like I said, there are two versions of the safe now, which is the pre money and the post money.

Maybe we'll quickly dive into those. So pre money is basically you and I, me being the investor, you being the founder in this scenario, you and I decide on what the company is valued at before any new money comes into the business. Pre money, right? Before money comes in, pre money. Post money is we decide what the valuation of the business will be after all the money has come in.

So, post money coming in, right? Fairly simple. Sounds simple until you try to do math around it. If we're talking about like, which one is, like, you'll probably hear terms like founder friendly, investor friendly a lot, right? I don't know if there's like a neutral friendly, but

Maxine 30:27 Everyone friendly. We all win.

Everyone friendly! The rainbow term. Friends!

Cheryl 30:35 No.

Cheryl and Maxine 30:36 We can be friends after we do the

Cheryl 30:38 deal. Uh, anyway. The Post money is more investor friendly, so often I will hear from investors saying that they prefer to do the post money safe because it means that they get more certainty around how much equity they are going to get.

It does mean that there is more dilution for the founder, which is why it is considered less founder friendly, versus the pre money is more founder friendly because it means that the founder is, gets a bit more clarity around, actually what, why is it more founder friendly Maxine? It's just less dilution for them.

Maxine 31:13 Oh yeah, less dilution.

Because, because what will happen, let's say you have a pre money of 5 million, if you raise 500, 000, or if you raise a million on top of that, all of the dilution is coming in to the investors. So the dilution that the amount of the, that the founder is taking is kind of set, and then the investors take the rest of that dilution.

Ultimately, the founder will be diluted because when it converts in that whole thing is diluting everyone down, but you're essentially think of it like a stack on where who's getting diluted when at the point that all of this prior contractual could. agreement converts into equity in the business.

Cheryl 31:49 That's one of the things you have to decide is, well, actually first pre money and post money. Then the next thing you have to decide is like what that valuation is regardless of whether it's pre money or post money. Then the next one or two things you need to decide are, and they're basically the only two key terms of a safe note, which is a, either a discount or a valuation cap.

Sometimes we see both. Actually, no. A lot of times in Australia we see both, which is interesting because in the US, especially with those two YCSafes, they don't have a template that is both. It is either or.

Maxine 32:20 This feels like double dipping for me. This gets me hot under the collar to see and talk about.

But yes, let's talk about them and I will become hot under the collar.

Cheryl and Maxine 32:30 All right, let's, let's first, let's define, let's define, uh, the VALCAP.

Maxine 32:36 Essentially, the VALCAP is the, they call it the implied valuation. So it's essentially the investor saying we think that this is how much the company is worth. And if we, if you raise At your next valuation.

So the price round is this or higher. We are only gonna convert in at this price. So tactical example, the $5 million post money I mentioned before. So you have a safe round. The val cap agreed is 5 million post money, let's say in a year and a half. That company then raises at. Say a 20 million post valuation, just for the niceness to my mental math here, then those safes are going to convert in as if they bought shares.

At a enterprise value of 5 million, and then they will get diluted by the additional capital coming in. And then they will get priced up to the new 20 million valuation. So that is your ValCap. You're essentially saying that is the cap at which I am converting in, in the scenario where the next round, the company raises at a valuation of say 3 million.

So it's a down round. You no longer have the benefit of the cap. I, you're not going to be converting it at 5 million when new investors are paying three. So as an investor, you just convert in at that three price, or if you have the discount. So as you mentioned, it's either, or in the U S so, or if you have the discounts or the terms are, you're just getting a 10 percent or 20 percent discount on whatever that next round.

is. So if you have the discount term in, then you would have a scenario where your, let's say it's a 10 percent discount. Then instead of having the benefit of the 5 million cap, you might have the benefit at that discount. So you get in at 2. 7, say on a 3 million round, and the new investors are coming in at 3 million and you're just getting that.

Discount difference. I wonder if it's a helpful jumping off point for you to describe what is a discount?

Cheryl 34:43 Yes, so, uh, the discount is basically a percentage amount and in documents, fun fact, you may see discount rate and that is Basically the full amount that you'll get versus the discount, which is the percentage off the full amount

For example, let's say I am investing in a company and the discount is 20%. Then let's say they raise under the cap or there was no cap, and the valuation at the time that they're doing a priced round is 5 million and my discount is 20%. Then my. equity holding would convert into shares at a four million dollar valuation and I would get essentially additional shares, 20 percent more shares than the investors who are currently buying in.

Now in that scenario the discount rate is 80% And the discount is 20. We actually, I have seen more terms than I think the founders would like to admit of where that has been mixed up. And the founder has reached back out to us and being like, Hey, can I actually edit

Cheryl and Maxine 35:53 that document? Cause it

Cheryl 35:54 says discount at 80 percent when it shows a discount.

Right. So like, and of course, you know, any sane investors like, yeah, obviously we We all kind of knew what that was meant to say, um, but it is a bit confusing.

Maxine 36:06 Yeah, that is super confusing. So I will say I've seen out there as well. I mean, in Australia, as you mentioned, the Australian investors, and I think this is set by the AIC.

I think that the AIC kind of normalized this, that investors get kind of both downside and upside protection because they put them both in there. It's like either or, whereas in the U. S. You have to choose at the outset. You either get the discount, so you're locking in a 10 or 20 percent discount, or you get the cap, and so you've got to hope that you're going to clear that cap when you race that next round.

Do you want to explain?

Cheryl 36:37 Yeah, whereas like, I'd say the vast majority, like 90 percent of the safes. that we've seen in Australia tend to have both as in they have a ValCap and they have a discount, which to be honest, I think is kind of a little, uh, unfair on the founders, but I mean, good for me as an investor personally, I think that will fade away and we will be more aligned to having to choose one or the other from the outset.

But typically what we see is that there is both, which means that investors get a reward for investing early, regardless of whether the founder invests.

I think the scenario where the founder ends up raising under the Valcap later on and then gets the additional dilution because investors get a discount, especially when it's at a higher discount rate, like 20 to 25%. You know, to 30. I think that makes it really tough to keep the founder motivated in the long run because of the dilution that they're taking.

And so I think the concern there for me as an investor, if they're offering both, and then in the worst case scenario, they, they end up raising a lot less, uh, raising an evaluation that's a lot less in the future, then I think it hurts the chances of that company being successful in the long run, which is why I think it's important as an investor to be conscious of those numbers and it's not necessarily always about getting the best deal because that doesn't necessarily equal the best outcome in the long run for you.

Maxine 38:03 Right. Which, I mean, I, Anne Marico is credited, uh, for a bit of advice that she kind of shared around the ecosystem, which I think is really interesting, which is at the very earliest stage. So where floodgate. There's no such thing as a good deal. There's just great companies. And so, you know, focusing on making sure you're not kind of nickel and diming at this early stage and really focusing on where that this company is building kind of an exceptional idea in an exceptional space with an exceptional team is much more important than thinking, you know, you're getting a steal and should be focusing on that.

That's an interesting one. Controversial. There's no

Cheryl 38:41 good deals, only great companies. Like, I don't know. I would, I would like, I would maybe devil's advocate that one a little bit. Like there are deals that I would do. And then there are deals that like, yeah, I believe in it, but I just don't think that that valuation is worth it this time.

But I think you're a great company. Actually, no opposite. Cause you know what? Fair enough. In that scenario, especially at the early stage, it's like, If it's a, if it's a, if it's a really spicy valuation, but I still think it's a great company, then like, why wouldn't I at the earlier stages? But I think on the opposite end, if it's a company that I'm a little bit unsure of, but it's a really good deal, as in like, it's a decent valuation, it's their first round, like, Super risky.

I'm not so confident on the founder that a little bit of a wild card, there's like some, you know, maybe the founding team doesn't have as much as I'd like them to have, um, or I can't quite see a path to a huge market, but there's something there, but it's a good deal. I'd probably still take that. Like,

Maxine 39:39 yeah, I mean, I think like the rational part of me is like, Yeah, that makes sense.

You feel like you're being compensated for the additional risk you're taking, right? You're like, you're taking execution risk, for example, if it's the first company that the founders ever built. Or you're taking market risk if it's like a particularly harebrained idea, you know? So I think provided you have the discipline there.

Having said that, I think it can be a real psychological trap to say, Oh, I don't have conviction on this company. So I'm just going to pay less for it. Yeah. I see that. And therefore it will be a better company. The guidance is like, that's not, that's very unlikely to materialize. Um, the other thing that I would say is that.

From what I've seen, especially for us, right, obviously, uh, at Coventures, we're really focused on accelerating companies internationally. So ideally, and most of the time, the investors that follow on after us, and sometimes even the investors that are coming in alongside us, uh, are U. S. based investors, and it is a.

Red flag for them. If the founder has sold too much of their company at too low of a valuation, because it makes them ask the question, kind of how sophisticated is this team? Are they peers with the group of people that we look to back day in day out? I kind of us based and definitely West coast based teams.

And are they plugged into those ecosystems? They having those conversations, essentially, why aren't they able to raise from those funds now, you and I both know that that is. Not the right way to be thinking about it, but it definitely comes up. So I will hear quite frequently investors in the U S ask me the question.

They'll do the kind of conversion from AUD to USD. And then they'll be like, hold on a second. They raise a 3 million USD post money for their pre seed. And now they're out in market in the U S looking for, you know, a nice spicy 25 to 30 million seed. Like. Which if we got in, I'm into it. Right. They're like, kudos to you for being in.

But like, that feels like a big jump. Like what, what are we missing there? Et cetera. Like for Australian investors that are looking to. Uh, support companies as they grow internationally and for Australian founders who are raising domestically. An interesting tight walk you have to make is how this valuation looks both domestically but also internationally to other investors.

Cheryl 41:59 The key point here is that like it's not always about getting the best deal for yourself and current investors because it doesn't always work out for you in the long run. You have to walk that tight rope. Absolutely. Uh, one other thing I might just say on the safe notes, what's really interesting is that last year's cut through venture survey found that 44 percent of startups, Australian startups, sorry, had safes on issue versus a startup survey that was conducted by cores in 2018 found that only 8%.

Had safe sign issue, which is a huge jump. Wow, that's huge. Like, this is a security that has gone up like crazy in the last, what is that, six years?

Maxine 42:39 Yeah, that is, wait, did you say 2008 or 2018? 2018. Wow. That is a material, I would, I would also expect it's going to accelerate. I reckon there's probably a bunch that.

stepped into the ecosystem in 24 as well. I think a lot of bridge rounds were done on some of these and that's just safe notes, right? That's not convertible notes or is that both? No, no, this is just safes. Wow. Wow. That's incredible.

Cheryl 43:00 Yeah, Con notes have gone down, uh, significantly. I don't know the exact number cause the, um, the other survey didn't quote those, but like anecdotally, I can tell you that we, we have seen less and less con notes over the years.

Maxine 43:13 Yeah, I find them a fairly awkward, um, like if you were choosing between safe and con note, I just, as a founder, I just don't know why you would go for a con note over a safe. I struggled to come up with a single reason other than your investor insists on a con note. Because. of the debt portion.

Cheryl 43:31 Yeah, I still know a few investors that insist on condos because they don't trust safes.

Maxine 43:37 Boo! So the last thing to say on safes before we move on to condos, but this is the case for both of them, is that they are not the purchase of equity and therefore they do not qualify you for the ESIC stuff as an investor.

Cheryl 43:53 Yes, yes, yes. The unsafe adventures of safes, uh, in that you only get the early stage innovation.

Company tax benefits when you actually acquire those shares and buying Investing by a safe or con note. You are not actually buying shares. You are buying the right to future shares So if the company qualifies at the time when you invest on that safe, it doesn't actually matter. They do the test When you actually acquire those shares, which can be really shitty.

Um, we kind of covered this in another episode. So if you want to dive into what ESIC is and what those tax benefits are, then please jump into our tax benefits, ESIC podcast episode. I don't know if that's the name for it, but.

Maxine 44:36 I hope it's not. I really hope that is not how we marketed that, but we'll link to it in the show notes and you can find it there.

Cheryl 44:43 It's in the list. Cool. Con notes. I don't think we've got to go super deep into con notes because personally I'd rather get onto like what's investor friendly versus not investor friendly. And we're running out of time here, but I think con notes is basically just like, it's the old kind of old school, old white guy version of.

The safe note, which just has an extra term, which is a maturity has two extra terms, a maturity date and a interest rate.

Maxine 45:11 Yeah, exactly. So kind of on the technicality side, it means that at a certain point, if you haven't raised another round, so it hasn't converted through then instead it just turns into a form of debt and you have to start paying that debt at a Pre agreed interest rate.

Cheryl 45:26 Yeah. I have seen some safes with maturity dates, by the way. Oof. You know, my thoughts on these, I think they stink. I was going to say, now that we're getting into like founder friendly versus not versus investor friendly, a maturity date on a safe note is decidedly. Uh, investor friendly.

Maxine 45:48 I just don't even, I don't think it helps anyone.

I think it is such a dumb, dumb term. Please, for the nerds out there, anyone please tell me the scenario in which this serves either the investor or the founder. There is a company in the U. S. that raised one round on a safe and has never raised again and just pays out dividends to the Very small number of founders slash one or two other investors that went in directly.

Actually, maybe not at all. They just pay out dividends to the founders. Uh, the SAFE has never converted to shares and blatantly have said we're not going to. We use the money to grow and become profitable and y'all can go get stuffed.

Maxine 46:34 That is savage. And I mean, I can understand it as an investor protection, but I would say like, how many deals did we do in 23?

I think I saw somewhere there's something like 2 million companies. Software companies like startups globally that are under 10 years old. And we can name a single time that this has happened, right? The alternative, which is the vast majority of circumstances where I have seen this play out, is you put a maturity date on the safe, right?

Something that we actually didn't double click on. The key term of a safe is its conversion clause. So essentially in the scenario that the company raises future capital, there is So these either a safe or a con note convert into equity, uh, using the inputs to a formula, i. e. the cap or the discount. So if that doesn't happen, thinking about raising a pre seed or seed, very few companies are coming into profitability any time before that conversion happens.

And so what it means is if the company hasn't raised another round within that maturity date. Then in theory, those investors can force the company to have to convert those safes into equity, which means that company then has to incur all of the legal costs of putting in place the shareholders agreement, you know, the constitution, if they need to do their own one, the subscription agreement, et cetera, plus they have to negotiate from a position of weakness because there's no round new investor coming in kind of setting terms.

And so they have to negotiate, kind of push and pull on each of these key terms in these documents with the investors. And it just gets very messy. No one can force a certain timeline. There's very rarely a timeline set to these clauses. So it's just like, you have to convert, go do. And it just gets messy, relationships break down.

And I, to be honest with you, if you've put a maturity date on that safe and the company hasn't been able to convert. That's safe in 24 to 36 months, like the probability that there is anything even worth converting into is extremely low. And so I think it just creates an enormous amount of pain and friction unnecessarily.

And you're better off just recognizing the investment model is what it was, which is. You know, this is a very risky asset class. We expect 50 percent of the companies we invest in to go to zero. If your company hasn't converted in 36 months, sometimes 48, sometimes 56, like it's probably not converting.

Cheryl 49:07 Interesting. I mean, I have actually seen maturity dates on safes in Australia fairly often. Like I have a more romanticized view of it in that like where we see it typically is like it just says it will convert at the Val cap that is listed. Like straight, so no discount on that, just it converts at the valcap, and Uh, no changes to the shareholders agreement.

So it presumes that there is a shareholders agreement in place in place already and that the investors were already happy with it and that the founder and investors also agree that that valuation cap that was set is the right valuation sometime in the future. So like in that. Scenario, I feel, I don't feel as strongly about this as you do.

Maxine 49:53 I feel better about it. You feel better about it? Yeah, okay. Yeah, if it's like a nice clean mechanic, right? Like the if this, then that, I'm not going to force you to the negotiating table. I'm not going to force you to, like, change terms, fine. But if it's like, I'm going to force you to the negotiating table when I have all of the leverage.

And when you're probably in the most vulnerable part of trying to survive. I have big problems with that.

Cheryl 50:15 And this is where I think Australia's government didn't quite think through a number of the mechanics in, uh, when they came up with ESIC. But the argument that I very much agree with is because of that trick where you don't actually get the ESIC benefit until it converts.

If a startup is about to, uh, trip the wire on not being an ESIC qualifying company anymore, Uh, over the financial year, uh, it can be more beneficial for an investor to say, Hey, can we actually convert from the safe to shares right now before we go into the next financial year? And before you become not easy, because, like, I believe that you are valued at what we set the cap at and that's what we're You know, you're going to raise it something similar to that in the next 12 months anyway, and I would much rather get my CGT tax benefit and be CGT free in the future when you exit.

That will be much more better outcome for me. So like, I see the argument there and Like, I don't know how they, I'm not sure how the Australian government, other than actually what they should have done is just account for saves, but like some rules around, you know, forcing that in a nice way could have been accounted for.

I don't know. That's the scenario that I see that it plays out.

Maxine 51:31 Yeah. Uh, yeah. I, I can see that scenario as well.

Cheryl 51:35 Yeah. Other founder friendly or non, like investor friendly versus founder friendly terms that you see?

Maxine 51:43 Um, over 23 and 24, I think. I saw a few ratchet clauses or liquidity preferences. So those are popping up in side letters, essentially.

I actually don't see them at pre seed. I saw them seed and later. So essentially the mechanic on those is if the investor gets kind of pre locked in. At a certain degree of return. So if there's a, say a two X liquidity preference, they're investing a million dollars, then they get to take 2 million out of the company in a liquidity event.

So a sale or an M&A before anyone else gets to participate. And so they guarantee that they will get at least a certain return. And then everything above that is gravy. That is, can be a disaster for founders and sometimes means that founders and the ESOP walk away with nothing. When, you know, a later investor has only come in fairly recently.

So, um, that one is particularly investor friendly.

Cheryl 52:34 I think the ones that, we kind of covered them a little bit earlier, but, like, worth noting that, like, pro rata rights, information rights, MFN, like, these are all more investor friendly terms, primarily because, They create more admin work for the founder, which again, anytime you're creating more admin work for the founder, it means less time they're focused on the company and puts restrictions in place that mean that their options for keeping the company alive are less.

Maxine 53:02 To be honest with you, I find the whole ecosystem very trust driven, right? Most of us are pretty repeat players. It's a very small ecosystem. So if you behave like a jerk, everyone finds out about it pretty quickly and they avoid you like the plague. And so I find most of these negotiations to be very civil.

I find most of these negotiations to be very reasonable on both sides, especially at the early stage, right? We're all aligned on the future value of the organization, as opposed to, you know, trying to nickel and dime over a single transaction at the earliest stage. So while we do see these. investor friendly and founder friendly terms.

Ultimately, they're still within like a reasonable range. They are.

Cheryl 53:42 Yeah. I think the last one to call out is that a higher ESOP is more investor friendly and the lower ESOP is more founder friendly because in the event that any unallocated ESOP goes back to shareholders, it can mean a bump in equity for the Everyone, including investors.

Maxine 54:01 Yeah. Great call out. Great call out. Well, I think that's it.

Cheryl 54:05 Yeah.

Maxine 54:06 We made it to the end. Hopefully you're still with us. Hopefully that gives you a good running start to the year. If you are thinking of investing, uh, this year, or you just want to brush up on your fundamentals.

Cheryl 54:17 But at the same time, we know that many of these concepts are complex and it can definitely help to have visuals and be able to read through real life examples.

So if you do want to solidify your understanding or if you're looking at a deal at the moment and want to sense check some of those terms, we definitely recommend doing the Angel Academy course. There's a whole section on detail structures and terms, including lots of examples and, uh, and diagrams of things.

That match other things and tables of founder friendly versus investor friendly. So go on over to www. venture. academy for that angel investing course.

Maxine 54:51 Enjoy the nerd out everyone. And we will see you out there.

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